TY - JOUR
T1 - One-pot synthesis of highly emissive dipyridinium dihydrohelicenes
AU - Santoro, Amedeo
AU - Lord, Rianne M.
AU - Loughrey, Jonathan J.
AU - McGowan, Patrick C.
AU - Halcrow, Malcolm A.
AU - Henwood, Adam F.
AU - Thomson, Connor
AU - Zysman-Colman, Eli
PY - 2015/5/4
Y1 - 2015/5/4
N2 - Condensation of a pyridyl‐2‐carbaldehyde derivative with 2‐(bromoethyl)amine hydrobromide gave tetracyclic pyrido[1,2‐a]pyrido[1′,2′:3,4]imidazo‐[2,1‐c]‐6,7‐dihydropyrazinium dications in excellent yields. Crystal structures and NOE data demonstrated the helical character of the dications, the dihedral angles between the two pyrido groups ranging from 28–45°. An intermediate in the synthesis was also characterized. A much brighter emission compared to literature helicenes has been found, with quantum yields as high as 60 % in the range of λ=460–600 nm. Preliminary cytotoxicity studies against HT‐29 cancer cells demonstrated moderate‐to‐good activity, with IC50 values 12–30× that of cisplatin.
AB - Condensation of a pyridyl‐2‐carbaldehyde derivative with 2‐(bromoethyl)amine hydrobromide gave tetracyclic pyrido[1,2‐a]pyrido[1′,2′:3,4]imidazo‐[2,1‐c]‐6,7‐dihydropyrazinium dications in excellent yields. Crystal structures and NOE data demonstrated the helical character of the dications, the dihedral angles between the two pyrido groups ranging from 28–45°. An intermediate in the synthesis was also characterized. A much brighter emission compared to literature helicenes has been found, with quantum yields as high as 60 % in the range of λ=460–600 nm. Preliminary cytotoxicity studies against HT‐29 cancer cells demonstrated moderate‐to‐good activity, with IC50 values 12–30× that of cisplatin.
UR - http://www.scopus.com/inward/record.url?eid=2-s2.0-84928383892&partnerID=MN8TOARS
U2 - 10.1002/chem.201406255
DO - 10.1002/chem.201406255
M3 - Article
VL - 21
SP - 7035
EP - 7038
JO - Chemistry-A European Journal
JF - Chemistry-A European Journal
SN - 0947-6539
IS - 19
ER -
